Dumber than Dumb: Stupider than Stupid

You decide to talk to people. You haven't had a consistent dialogue with anyone for a long time. Your conversation skills, below average, depart from the norm dramatically. On the 2nd of May, while walking down the stupid, bustling streets of Stupid Trading District on one of your daily wanders with pennies jiggling in your pocket, you are confronted face-to-face with a man who is just about as stupid as you. He seems to be old with a scraggly white beard and sharp eyebrows.

What should you talk to him about?